Methylglyoxal → HCID 11298738, compound

HRID 1443026Notes

Reaction equation

HRID 1443026 reaction equation
[CH:1](=O)[C:2]([CH3:4])=O.O.[NH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][NH2:16].N1[C:21]2C=CC=C[C:20]=2N=N1.C(C=O)=O.[BH4-].[Na+]>O.C(O)C>[CH3:4][C:2]12[CH:1]3[N:7]4[CH2:20][CH2:21][N:16]3[CH2:15][CH2:14][N:13]1[CH2:12][CH2:11][N:10]2[CH2:9][CH2:8]4

Participants

8

Reactant 5

HCID 880MethylglyoxalHCID 7860GlyoxalHCID 4311764Sodium borohydrideHCID 16211736N~1~,N~1'~-(Ethane-1,2-diyl)di(ethane-1,2-diamine)--water (1/1)HCID 178418385HCID 178418385, compound

Product 1

HCID 11298738HCID 11298738, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Conditions

Temperature
2 °C

Procedure

A 40% strength solution of 61.56 g of pyruvaldehyde in water (342 mmol) in 100 ml of water is added by slow dropwise addition INto a solution of 60.66 g (342 mmol) of triethylenetetraamine hydrate (containing 17% water) in 300 ml of distilled water cooled to 2° C. On completion of addition, the reaction mixture is adjusted to ambient temperature and 81.40 g (684 mmol) of benzotriazole are added in a single portion. 300 ml of ethanol are then added to the reaction medium, then a solution of 49.59 g of glyoxal (40% in water) (342 mmol) in 100 ml of ethanol is added by slow dropwise addition. After 2 h of stirring at ambient temperature, the solution is cooled to 0° C. and 25.87 g (684 mmol) of NaBH4 are added in small portions. After returning to ambient temperature, the reaction medium is stirred for 2 h, the ethanol is evaporated and 70 g of KOH pellets are added to the residue. The solution is then extracted with two 1 l portions of chloroform. After drying over MgSO4 and evaporation of the solvents, (IIb) is isolated in the form of an orange oil (32.3 g; yield=45%).

Workup

  1. additionOn completion of addition
  2. customis adjusted to ambient temperature
  3. temperaturethe solution is cooled to 0° C.
  4. customAfter returning to ambient temperature
  5. stirringthe reaction medium is stirred for 2 h
  6. customthe ethanol is evaporated
  7. addition70 g of KOH pellets are added to the residue
  8. extractionThe solution is then extracted with two 1 l portions of chloroform
  9. dry with materialAfter drying over MgSO4 and evaporation of the solvents
  10. custom(IIb) is isolated in the form of an orange oil (32.3 g; yield=45%)

Sources & evidence

ORD record
ord-9efa181e732746a3affeacdd79704546
Source dataset
uspto-grants-2010_02
Patent number
US07659393B2

Reaction notes

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